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Q. The electrophile, $E^{+}$ attacks the benzene ring to generate the intermediate $\sigma$ -complex. Of the following, which $\sigma$ -complex is of lowest energy?

Organic Chemistry – Some Basic Principles and Techniques

Solution:

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This structure will be of lowest energy due to resonance stabilisation of $+ve$ charge. In all other three structures, the presence of electron-withdrawing $NO _{2}$ group will destabilize the $+ve$ charge and hence they will have greater energy.